The Road to Middle-earth explores J.R.R. Tolkien's creativity and the sources of his inspiration. Shippey shows in detail how Tolkien's professional background led him to write The Hobbit and how he created a timeless charm for millions of readers. Examining the foundation of Tolkien's most popular work, The Lord of the Rings, Shippey also discusses the contribution of The Silmarillion and Unfinished Tales to Tolkien's great myth cycle, showing how Tolkien's more "difficult" books can be fully appreciated. He goes on to examine the remarkable twelve-volume History of Middle-earth, written by Tolkien's son and literary heir Christopher Tolkien, which traces the creative and technical processes by which Middle-earth evolved.

It was not till 1972 that I met Tolkien in person, by which time I had been promoted from Birmingham to a Fellowship at St. John’s College, Oxford, to teach Old and Middle English along the lines which Tolkien had laid down many years before. Just after I arrived in Oxford, Tolkien’s successor in the Merton Chair of English Language, Norman Davis, invited me to dine at Merton and meet Tolkien, who was then living in college lodgings following the death of his wife. The meeting left me with a strong sense of obligation and even professional piety, in the old sense of that word, i.e. ‘affectionate loyalty and respect, esp. to parents’, or in this case predecessors. After Tolkien’s death I felt increasingly that he would not have been happy with many of the things people said about his writings, and that someone with a similar background to his own ought to try to provide—as Tolkien and E. V. Gordon wrote in the ‘Preface’ to their 1925 edition of Sir Gawain and the Green Knight—‘a sufficient apparatus for reading [these remarkable works] with an appreciation as far as possible of the sort which its author may be supposed to have desired’.